Density functional study of the electronic structure of dye-functionalized fullerenes and their model donor-acceptor complexes containing P3HT

Baruah, Tunna; Garnica, Amanda; Paggen, Marina; Basurto, Luis; Zope, Rajendra R.

doi:10.1063/1.4944469

Density functional study of the electronic structure of dye-functionalized fullerenes and their model donor-acceptor complexes containing P3HT

Journal Article · Fri Apr 08 00:00:00 EDT 2016 · Journal of Chemical Physics

DOI:https://doi.org/10.1063/1.4944469· OSTI ID:1469583

Baruah, Tunna ^[1]; Garnica, Amanda ^[2]; Paggen, Marina ^[2]; Basurto, Luis ^[2]; Zope, Rajendra R. ^[2]

Univ. of Texas, El Paso, TX (United States). Dept. of Physics; University of Texas at El Paso
Univ. of Texas, El Paso, TX (United States). Dept. of Physics

Here, we study the electronic structure of C₆₀ fullerenes functionalized with a thiophene-diketopyrrolopyrrole-thiophene based chromophore using density functional theory combined with large polarized basis sets. As the attached chromophore has electron donor character, the functionalization of the fullerene leads to a donor-acceptor (DA) system. We examine in detail the effect of the linker and the addition site on the electronic structure of the functionalized fullerenes. We further study the electronic structure of these DA complexes with a focus on the charge transfer excitations. Finally, we examine the interface of the functionalized fullerenes with the widely used poly(3-hexylthiophene-2,5-diyl) (P3HT) donor. Our results show that all functionalized fullerenes with an exception of the C₆₀-pyrrolidine [6,6], where the pyrrolidine is attached at a [6,6] site, have larger electron affinities relative to the pristine C₆₀ fullerene. We also estimate the quasi-particle gap, lowest charge transfer excitation energy, and the exciton binding energies of the functionalized fullerene-P3MT model systems. Results show that the exciton binding energies in these model complexes are slightly smaller compared to a similarly prepared phenyl-C₆₁-butyric acid methyl ester (PCBM)-P3MT complex.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of Texas, El Paso, TX (United States)

Sponsoring Organization:: National Science Foundation (NSF); USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Contributing Organization:: Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). National Energy Research Scientific Computing Center (NERSC)

Grant/Contract Number:: SC0002168; SC0006818

OSTI ID:: 1469583

Alternate ID(s):: OSTI ID: 1246532
OSTI ID: 22657907

Journal Information:: Journal of Chemical Physics, Journal Name: Journal of Chemical Physics Journal Issue: 14 Vol. 144; ISSN JCPSA6; ISSN 0021-9606

Publisher:: American Institute of Physics (AIP)Copyright Statement

Country of Publication:: United States

Language:: English

References (59)

Origin of the Open Circuit Voltage of Plastic Solar Cells Brabec, C. J.; Cravino, A.; Meissner, D. Advanced Functional Materials, Vol. 11, Issue 5 https://doi.org/10.1002/1616-3028(200110)11:5<374::AID-ADFM374>3.0.CO;2-W	journal	October 2001
Electron Trapping in Higher Adduct Fullerene-Based Solar Cells Lenes, Martijn; Shelton, Steve W.; Sieval, Alex B. Advanced Functional Materials, Vol. 19, Issue 18 https://doi.org/10.1002/adfm.200900459	journal	September 2009
Effects of Fullerene Bisadduct Regioisomers on Photovoltaic Performance Meng, Xiangyue; Zhao, Guangyao; Xu, Qi Advanced Functional Materials, Vol. 24, Issue 1 https://doi.org/10.1002/adfm.201301411	journal	July 2013
Fullerene Bisadducts for Enhanced Open-Circuit Voltages and Efficiencies in Polymer Solar Cells Lenes, Martijn; Wetzelaer, Gert-Jan A. H.; Kooistra, Floris B. Advanced Materials, Vol. 20, Issue 11, p. 2116-2119 https://doi.org/10.1002/adma.200702438	journal	June 2008
Narrow‐Bandgap Diketo‐Pyrrolo‐Pyrrole Polymer Solar Cells: The Effect of Processing on the Performance Wienk, Martijn M.; Turbiez, Mathieu; Gilot, Jan Advanced Materials, Vol. 20, Issue 13, p. 2556-2560 https://doi.org/10.1002/adma.200800456	journal	July 2008
Bulk Heterojunction Solar Cells with Large Open-Circuit Voltage: Electron Transfer with Small Donor-Acceptor Energy Offset Gong, Xiong; Tong, Minghong; Brunetti, Fulvio G. Advanced Materials, Vol. 23, Issue 20 https://doi.org/10.1002/adma.201003768	journal	March 2011
Efficient Methano[70]fullerene/MDMO-PPV Bulk Heterojunction Photovoltaic Cells Wienk, Martijn M.; Kroon, Jan M.; Verhees, Wiljan J. H. Angewandte Chemie International Edition, Vol. 42, Issue 29 https://doi.org/10.1002/anie.200351647	journal	July 2003
Opening and Closure of the Fullerene Cage incis-Bisimino Adducts of C60: The Influence of the Addition Pattern and the Addend Schick, Georg; Hirsch, Andreas; Mauser, Harald Chemistry - A European Journal, Vol. 2, Issue 8 https://doi.org/10.1002/chem.19960020807	journal	August 1996
Why Do Cycloaddition Reactions Involving C ₆₀ Prefer [6,6] over [5,6] Bonds? Fernández, Israel; Solà, Miquel; Bickelhaupt, F. Matthias Chemistry - A European Journal, Vol. 19, Issue 23 https://doi.org/10.1002/chem.201300648	journal	April 2013
Improved Purification of C60 and Formation of ?- and ?-Homoaromatic methano-bridged fullerenes by reaction with alkyl diazoacetates Isaacs, Lyle; Wehrsig, Arno; Diederich, Fran�ois Helvetica Chimica Acta, Vol. 76, Issue 3 https://doi.org/10.1002/hlca.19930760310	journal	May 1993
A renaissance of color: New structures and building blocks for organic electronics Robb, Maxwell J.; Ku, Sung-Yu; Brunetti, Fulvio G. Journal of Polymer Science Part A: Polymer Chemistry, Vol. 51, Issue 6 https://doi.org/10.1002/pola.26531	journal	January 2013
Organic Photovoltaics Brabec, Christoph J.; Dyakonov, Vladimir; Parisi, Jürgen Springer Series in Materials Science https://doi.org/10.1007/978-3-662-05187-0	book	January 2003
Observation of a photoinduced electron transfer from a conducting polymer (MEHPPV) onto C60 Sariciftci, N. S.; Smilowitz, L.; Braun, D. Synthetic Metals, Vol. 56, Issue 2-3 https://doi.org/10.1016/0379-6779(93)90090-J	journal	April 1993
Semiconducting polymers (as donors) and buckminsterfullerene (as acceptor): photoinduced electron transfer and heterojunction devices Sariciftci, N. S.; Smilowitz, L.; Heeger, A. J. Synthetic Metals, Vol. 59, Issue 3 https://doi.org/10.1016/0379-6779(93)91166-Y	journal	August 1993
The influence of materials work function on the open circuit voltage of plastic solar cells Brabec, C. J.; Cravino, A.; Meissner, D. Thin Solid Films, Vol. 403-404 https://doi.org/10.1016/S0040-6090(01)01586-3	journal	February 2002
Hydrogen-bonded diketopyrrolopyrrole (DPP) pigments as organic semiconductors Głowacki, Eric Daniel; Coskun, Halime; Blood-Forsythe, Martin A. Organic Electronics, Vol. 15, Issue 12 https://doi.org/10.1016/j.orgel.2014.09.038	journal	December 2014
The effect of thiophene substituents of fulleropyrrolidine acceptors on the performance of inverted organic solar cells Kaunisto, Kimmo M.; Subbaiyan, Navaneetha K.; K. C., Chandra Bikram Synthetic Metals, Vol. 195 https://doi.org/10.1016/j.synthmet.2014.06.007	journal	September 2014
An unprecedented [5,6]-open adduct via a direct benzyne-C60 cycloaddition Kim, Gyoungsik; Lee, Kyu Cheol; Kim, Jonggi Tetrahedron, Vol. 69, Issue 35 https://doi.org/10.1016/j.tet.2013.06.073	journal	September 2013
[60]Fulleropyrrolidines Bearing π-Conjugated Moiety for Polymer Solar Cells: Contribution of the Chromophoric Substituent on C ₆₀ to the Photocurrent Saravanan, Chinnusamy; Liu, Che-Liang; Chang, Yi-Min ACS Applied Materials & Interfaces, Vol. 4, Issue 11 https://doi.org/10.1021/am301773t	journal	November 2012
Synthesis of Novel Acceptor Molecules of Mono- and Multiadduct Fullerene Derivatives for Improving Photovoltaic Performance Liu, Chao; Xu, Liang; Chi, Dan ACS Applied Materials & Interfaces, Vol. 5, Issue 3 https://doi.org/10.1021/am3028475	journal	January 2013
Electrochemistry of Fullerenes and Their Derivatives Echegoyen, Luis; Echegoyen, Lourdes E. Accounts of Chemical Research, Vol. 31, Issue 9, p. 593-601 https://doi.org/10.1021/ar970138v	journal	September 1998
Fulleropyrrolidines: A Family of Full-Fledged Fullerene Derivatives Prato, Maurizio; Maggini, Michele Accounts of Chemical Research, Vol. 31, Issue 9 https://doi.org/10.1021/ar970210p	journal	September 1998
Conjugated poly(thiophenes): synthesis, functionalization, and applications Roncali, Jean Chemical Reviews, Vol. 92, Issue 4 https://doi.org/10.1021/cr00012a009	journal	June 1992
DFT Calculations on Charge-Transfer States of a Carotenoid-Porphyrin-C ₆₀ Molecular Triad Baruah, Tunna; Pederson, Mark R. Journal of Chemical Theory and Computation, Vol. 5, Issue 4 https://doi.org/10.1021/ct900024f	journal	March 2009
Synthesis of a rigid "ball-and-chain" donor-acceptor system through Diels-Alder functionalization of buckminsterfullerene (C60) Khan, Saeed I.; Oliver, Anna M.; Paddon-Row, Michael N. Journal of the American Chemical Society, Vol. 115, Issue 11 https://doi.org/10.1021/ja00064a075	journal	June 1993
Energetic preference in 5,6 and 6,6 ring junction adducts of C60: fulleroids and methanofullerenes Prato, Maurizio; Lucchini, Vittorio; Maggini, Michele Journal of the American Chemical Society, Vol. 115, Issue 18 https://doi.org/10.1021/ja00071a080	journal	September 1993
Photochemical Fulleroid to Methanofullerene Conversion via the Di-.pi.-methane (Zimmerman) Rearrangement Janssen, Rene A. J.; Hummelen, Jan C.; Wudl, Fred Journal of the American Chemical Society, Vol. 117, Issue 1 https://doi.org/10.1021/ja00106a068	journal	January 1995
Observation of Both Thermal First-Order and Photochemical Zero-Order Kinetics in the Rearrangement of [6,5] Open Fulleroids to [6,6] Closed Fullerenes Hall, Melvin H.; Lu, Huajun; Shevlin, Philip B. Journal of the American Chemical Society, Vol. 123, Issue 7 https://doi.org/10.1021/ja003042w	journal	February 2001
Why Is the Rearrangement of [6,5] Open Fulleroids to [6,6] Closed Fullerenes Zero Order? Li, Zizhong; Shevlin, Philip B. Journal of the American Chemical Society, Vol. 119, Issue 5 https://doi.org/10.1021/ja963088i	journal	February 1997
The Specific Acid-Catalyzed and Photochemical Isomerization of a Robust Fulleroid to a Methanofullerene Gonzalez, Rosario; Hummelen, Jan C.; Wudl, Fred The Journal of Organic Chemistry, Vol. 60, Issue 8 https://doi.org/10.1021/jo00113a049	journal	April 1995
[6-6]-Closed versus [6-5]-Open Isomers of Imino- and Methanofullerenes: A Comparison with Pristine C ₆₀ and (C ₅₉ N) ^• Guldi, Dirk M.; Hungerbühler, Hartmut; Carmichael, Ian The Journal of Physical Chemistry A, Vol. 104, Issue 38 https://doi.org/10.1021/jp0016838	journal	September 2000
Comparative Photophysics of C ₆₁ H ₂ Isomers ^† Anthony, Stephen M.; Bachilo, Sergei M.; Weisman, R. Bruce The Journal of Physical Chemistry A, Vol. 107, Issue 49 https://doi.org/10.1021/jp035085f	journal	December 2003
Absolute Rate of Charge Separation and Recombination in a Molecular Model of the P3HT/PCBM Interface Liu, Tao; Troisi, Alessandro The Journal of Physical Chemistry C, Vol. 115, Issue 5 https://doi.org/10.1021/jp109130y	journal	December 2010
PCBM Disperse-Red Ester with Strong Visible-Light Absorption: Implication of Molecular Design and Morphological Control for Organic Solar Cells Wang, Mingfeng; Chesnut, Eneida; Sun, Yanming The Journal of Physical Chemistry C, Vol. 116, Issue 1 https://doi.org/10.1021/jp209782c	journal	December 2011
A Low Band Gap, Solution Processable Oligothiophene with a Diketopyrrolopyrrole Core for Use in Organic Solar Cells Tamayo, Arnold B.; Walker, Bright; Nguyen*, Thuc-Quyen The Journal of Physical Chemistry C, Vol. 112, Issue 30 https://doi.org/10.1021/jp8031572	journal	July 2008
Design, Synthesis, and Self-assembly of Oligothiophene Derivatives with a Diketopyrrolopyrrole Core Tamayo, Arnold Bernarte; Tantiwiwat, Mananya; Walker, Bright The Journal of Physical Chemistry C, Vol. 112, Issue 39 https://doi.org/10.1021/jp804816c	journal	September 2008
Oligothiophene Derivatives Functionalized with a Diketopyrrolopyrrolo Core for Solution-Processed Field Effect Transistors: Effect of Alkyl Substituents and Thermal Annealing Tantiwiwat, Mananya; Tamayo, Arnold; Luu, Ngoc The Journal of Physical Chemistry C, Vol. 112, Issue 44 https://doi.org/10.1021/jp8068305	journal	October 2008
Role of Semiconducting and Metallic Tubes in P3HT/Carbon-Nanotube Photovoltaic Heterojunctions: Density Functional Theory Calculations Kanai, Yosuke; Grossman, Jeffrey C. Nano Letters, Vol. 8, Issue 3 https://doi.org/10.1021/nl0732777	journal	March 2008
Fulleropyrrolidine-containing sterically hindered phenol. Synthesis, structure, and properties Nuretdinov, I. A.; Gubskaya, V. P.; Yanilkin, V. V. Russian Chemical Bulletin, Vol. 50, Issue 4, p. 607-613 https://doi.org/10.1023/A:1011392207814	journal	January 2001
Fullerene derivative acceptors for high performance polymer solar cells He, Youjun; Li, Yongfang Phys. Chem. Chem. Phys., Vol. 13, Issue 6 https://doi.org/10.1039/C0CP01178A	journal	January 2011
Solution processable low bandgap diketopyrrolopyrrole (DPP) based derivatives: novel acceptors for organic solar cells Sonar, Prashant; Ng, Ging-Meng; Lin, Ting Ting Journal of Materials Chemistry, Vol. 20, Issue 18 https://doi.org/10.1039/b924404b	journal	January 2010
Diketopyrrolopyrrole (DPP)-based materials for organic photovoltaics Qu, Sanyin; Tian, He Chemical Communications, Vol. 48, Issue 25 https://doi.org/10.1039/c2cc17886a	journal	January 2012
Addition reactions of C60 leading to fulleroprolines Maggini, Michele; Scorrano, Gianfranco; Bianco, Alberto Journal of the Chemical Society, Chemical Communications, Issue 3 https://doi.org/10.1039/c39940000305	journal	January 1994
Electron deficient diketopyrrolopyrrole dyes for organic electronics: synthesis by direct arylation, optoelectronic characterization, and charge carrier mobility Hendsbee, Arthur D.; Sun, Jon-Paul; Rutledge, Lesley R. J. Mater. Chem. A, Vol. 2, Issue 12 https://doi.org/10.1039/c3ta14414c	journal	January 2014
A novel complementary absorbing donor–acceptor pair in block copolymers based on single material organic photovoltaics Koyuncu, Sermet; Wang, Hsin-Wei; Liu, Feng J. Mater. Chem. A, Vol. 2, Issue 9 https://doi.org/10.1039/c3ta14902a	journal	January 2014
Valence isomerism and rearrangements in methanofullerenes Diederich, Fran�ois; Isaacs, Lyle; Philp, Douglas Journal of the Chemical Society, Perkin Transactions 2, Issue 3 https://doi.org/10.1039/p29940000391	journal	January 1994
On the Non‐Orthogonality Problem Connected with the Use of Atomic Wave Functions in the Theory of Molecules and Crystals Löwdin, Per‐Olov The Journal of Chemical Physics, Vol. 18, Issue 3 https://doi.org/10.1063/1.1747632	journal	March 1950
A low band gap, solution processable oligothiophene with a dialkylated diketopyrrolopyrrole chromophore for use in bulk heterojunction solar cells Tamayo, Arnold Bernarte; Dang, Xuan-Dang; Walker, Bright Applied Physics Letters, Vol. 94, Issue 10 https://doi.org/10.1063/1.3086897	journal	March 2009
A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu Grimme, Stefan; Antony, Jens; Ehrlich, Stephan The Journal of Chemical Physics, Vol. 132, Issue 15 https://doi.org/10.1063/1.3382344	journal	April 2010
Charge transfer excited state energies by perturbative delta self consistent field method Baruah, Tunna; Olguin, Marco; Zope, Rajendra R. The Journal of Chemical Physics, Vol. 137, Issue 8 https://doi.org/10.1063/1.4739269	journal	August 2012
Investigation of photoexcitations of conjugated polymer/fullerene composites embedded in conventional polymers Brabec, C. J.; Dyakonov, V.; Sariciftci, N. S. The Journal of Chemical Physics, Vol. 109, Issue 3 https://doi.org/10.1063/1.476664	journal	July 1998
Small Bandgap Polymers for Organic Solar Cells (Polymer Material Development in the Last 5 Years) Kroon, Renee; Lenes, Martijn; Hummelen, Jan C. Polymer Reviews, Vol. 48, Issue 3 https://doi.org/10.1080/15583720802231833	journal	August 2008
Optimization of Gaussian basis sets for density-functional calculations Porezag, Dirk; Pederson, Mark R. Physical Review A, Vol. 60, Issue 4 https://doi.org/10.1103/PhysRevA.60.2840	journal	October 1999
Variational mesh for quantum-mechanical simulations Pederson, Mark R.; Jackson, Koblar A. Physical Review B, Vol. 41, Issue 11 https://doi.org/10.1103/PhysRevB.41.7453	journal	April 1990
Accurate forces in a local-orbital approach to the local-density approximation Jackson, Koblar; Pederson, Mark R. Physical Review B, Vol. 42, Issue 6 https://doi.org/10.1103/PhysRevB.42.3276	journal	August 1990
Infrared intensities and Raman-scattering activities within density-functional theory Porezag, Dirk; Pederson, Mark R. Physical Review B, Vol. 54, Issue 11 https://doi.org/10.1103/PhysRevB.54.7830	journal	September 1996
Generalized Gradient Approximation Made Simple Perdew, John P.; Burke, Kieron; Ernzerhof, Matthias Physical Review Letters, Vol. 77, Issue 18, p. 3865-3868 https://doi.org/10.1103/PhysRevLett.77.3865	journal	October 1996
Generalized Gradient Approximation Made Simple [Phys. Rev. Lett. 77, 3865 (1996)] Perdew, John P.; Burke, Kieron; Ernzerhof, Matthias Physical Review Letters, Vol. 78, Issue 7 https://doi.org/10.1103/PhysRevLett.78.1396	journal	February 1997
Photoinduced Electron Transfer from a Conducting Polymer to Buckminsterfullerene Sariciftci, N. S.; Smilowitz, L.; Heeger, A. J. Science, Vol. 258, Issue 5087, p. 1474-1476 https://doi.org/10.1126/science.258.5087.1474	journal	November 1992

Similar Records

Density functional study of the electronic structure of dye-functionalized fullerenes and their model donor-acceptor complexes containing P3HT

Journal Article · Thu Apr 14 00:00:00 EDT 2016 · Journal of Chemical Physics · OSTI ID:22657907

A New Model for the Morphology of P3HT/PCBM Organic Photovoltaics from Small-Angle Neutron Scattering: Rivers and Streams

Journal Article · Fri Dec 31 23:00:00 EST 2010 · ACS Nano · OSTI ID:1041095

Linking the HOMO-LUMO gap to torsional disorder in P3HT/PCBM blends

Journal Article · Sun Dec 13 23:00:00 EST 2015 · Journal of Chemical Physics · OSTI ID:22493328

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
74 ATOMIC AND MOLECULAR PHYSICS
bond length
chemical compounds and components
chemical elements
density functional theory
electrochemistry
electronic structure
excitation energies
excitons
fullerenes
leptons

Density functional study of the electronic structure of dye-functionalized fullerenes and their model donor-acceptor complexes containing P3HT

Citation Formats

References (59)

Similar Records

Related Subjects